(Z)-3-methyl-1-(tetrahydropyran-2-yloxy)hex-2-en-4-yne | 196616-18-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (Z)-3-methyl-1-(tetrahydropyran-2-yloxy)hex-2-en-4-yne
• CAS: 196616-18-9
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: ZMFGJQJBGPXJEZ-FLIBITNWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-3-methyl-1-(tetrahydropyran-2-yloxy)hex-2-en-4-yne 在 manganese(IV) oxide 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 3-methylhex-2-en-4-ynynal
  参考文献：
  名称：

  Palladium-Catalyzed Alkoxycarbonylation of (Z)-2-En-4-yn Carbonates Leading to 2,3,5-Trienoates

  摘要：

  Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.

  DOI：

  10.1021/ol102989q
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 正丁基锂 、 对甲苯磺酸 作用下， 以 正己烷 为溶剂， 反应 0.75h， 生成 (Z)-3-methyl-1-(tetrahydropyran-2-yloxy)hex-2-en-4-yne
  参考文献：
  名称：

  Palladium-Catalyzed Alkoxycarbonylation of (Z)-2-En-4-yn Carbonates Leading to 2,3,5-Trienoates

  摘要：

  Pd(0)-catalyzed carbonylation of (Z)-2-en-4-yn carbonates in the presence of a balloon pressure of CO in an alcohol donates vinylallenyl esters with an exclusively E-configuration and in high yields. The fact that no such reactivity could be observed with E-configured enyne carbonates may indicate that the reaction is promoted via the cooperative coordination of palladium with both alkynyl and carbonate moieties.

  DOI：

  10.1021/ol102989q

文献信息

• Radical Hydrostannylation, Pd(0)-Catalyzed Hydrostannylation, Stannylcupration of Propargyl Alcohols and Enynols:  Regio- and Stereoselectivities
  作者：Jean-François Betzer、Francette Delaloge、Benoît Muller、Ange Pancrazi、Joëlle Prunet

  DOI：10.1021/jo9710339

  日期：1997.10.1

  Different enynols and propargyl derivatives were sumitted to radical hydrostannylation (Bu3SnH/AIBN), Pd(0)-catalyzed hydrostannylation [Bu3SnH/Pd(0)], and stannylcupration [Bu3Sn(R)CuCNLi2] conditions. Except for the radical stannylation reaction, high regio-and stereoselective formation of vinyl-and dienylstannanes are obtained. Results are tentatively explained in terms of steric Interactions between the alkyne or enyne substituents and the palladium or cuprate moieties in the different reaction intermediates.